A Fruitful Retirement: Social Security Benefit Taking your Social Security benefits at the right time may help maximize your benefit. Related Content Three Key Questions to Answer Before Taking Social Security When to start? Should I continue to work? How can I maximize my benefit? Tax Deductions You Won't Believe Here are some examples of deductions from the IRS that were permitted and some that were, uh, too creative. Federal Income Tax Use this calculator to estimate your income tax liability along with average and marginal tax rates.